Bromide ion → HCID 57749423, compound

HRID 1162467Notes

Reaction equation

HRID 1162467 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7]([NH2:9])=[N:8][C:4]=2[CH:3]=1.F[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Br-]>O.CN(C)C(=O)C>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH2:9])[N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=3)[C:4]=2[CH:3]=1

Participants

7

Reactant 4

HCID 259Bromide ionHCID 97462-FluoropyridineHCID 10796Cesium carbonateHCID 178508148HCID 178508148, compound

Product 1

HCID 57749423HCID 57749423, compoundYield 26%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
150 °C

Procedure

To two 10-20 mL microwave vials was added 5-bromo-1H-benzo[d]imidazol-2-amine (3.00 g, 14.1 mmol, Carbocore, The Woodlands, Tex.), N,N-dimethylacetamide (20 mL), 2-fluoropyridine (1.46 mL, 17.0 mmol, Aldrich, St. Louis, Mo.) and cesium carbonate (7.84 g, 24.1 mmol). (One-half of the material in each vial, ie 1.5 g of the bromide in each vial.) The mixture was heated at 150° C. for 140 min in the microwave. After cooling to rt, the combined reaction mixtures were poured into water (400 mL) and then extracted with EtOAc/hexane (80:20) (3×150 mL). The combined extracts were washed with water (3×100 mL) and brine (100 mL) and then dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (0.5 to 3.8% MeOH (2 M in NH3)/CH2Cl2) afforded the title compound (1.06 g, 26%). MS (ESI, positive ion) m/z: 289 (M(79Br)+1).

Workup

  1. temperatureAfter cooling to rt
  2. customthe combined reaction mixtures
  3. extractionextracted with EtOAc/hexane (80:20) (3×150 mL)
  4. washThe combined extracts were washed with water (3×100 mL) and brine (100 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated onto silica
  7. customPurification by silica gel chromatography (0.5 to 3.8% MeOH (2 M in NH3)/CH2Cl2)

Sources & evidence

ORD record
ord-b030045f6cac40fc9fb56e437aabc5df
Source dataset
uspto-grants-2010_10
Patent number
US07820665B2

Reaction notes

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